WO2011007102A1 - Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid - Google Patents

Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid Download PDF

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WO2011007102A1
WO2011007102A1 PCT/FR2010/051486 FR2010051486W WO2011007102A1 WO 2011007102 A1 WO2011007102 A1 WO 2011007102A1 FR 2010051486 W FR2010051486 W FR 2010051486W WO 2011007102 A1 WO2011007102 A1 WO 2011007102A1
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acid
polyphenol
use according
omega
composition
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PCT/FR2010/051486
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French (fr)
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Michel De Lorgeril
Patricia Salen
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Universite Joseph Fourier (Grenoble 1)
Centre National De La Recherche Scientifique
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Priority to CA2768050A priority Critical patent/CA2768050A1/en
Priority to US13/383,290 priority patent/US20120202778A1/en
Priority to EP10752018A priority patent/EP2453888A1/en
Priority to AU2010272346A priority patent/AU2010272346A1/en
Publication of WO2011007102A1 publication Critical patent/WO2011007102A1/en

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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/158Fatty acids; Fats; Products containing oils or fats
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/111Aromatic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/116Heterocyclic compounds
    • A23K20/121Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12Fatty acids or derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • A61K31/20Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/202Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/3533,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/02Nutrients, e.g. vitamins, minerals
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates, in general, to the use of at least one omega-3 fatty acid and at least one polyphenol for the endogenous synthesis of eicosapentaenoic acid and docosahexaenoic acid.
  • human body and in particular supplementing this diet with a composition containing a mixture of at least one omega-3 fatty acid with a polyphenol for increasing the endogenous synthesis of omega-3 fatty acids at 20 or 22 carbon atoms (termed very long chain omega-3 fatty acids or TLC).
  • the main omega-3 fatty acids are ⁇ -linolenic acid or ⁇ 3 ⁇ (18: 3, ALA), eicosapentaenoic acid (20: 5, EPA) and docosahexaenoic acid (22: 6, DHA). They are called essential fatty acids because the animal body, especially human, does not know how to synthesize them or knows how to synthesize them in insufficient quantity. A minimal and regular intake of food is considered necessary by the experts.
  • TLC fatty acids including EPA and DHA
  • Nutritionists therefore recommend regular fish consumption. Nevertheless, the increase in fish consumption around the world is leading to overfishing and the desertification of the seas.
  • An alternative to overfishing is the existence of farmed fish on marine farms. Plankton containing significant amounts of DHA and EPA is essential for feeding farmed fish. The plankton is collected by the harvesters, which leads to the impoverishment of the seas. This chain of events is leading to ecological upheaval and violent conflict with the fish industry.
  • ALA is found in plants, but ALA is not efficiently transformed into TLC by animals, especially humans.
  • the use of ALA can not therefore, according to experts provide a lack of intake of omega-3 TLC of marine origin.
  • the present invention provides an alternative to the dietary consumption of TLC fatty acids of essentially marine origin.
  • the present invention relates to the use of at least one omega-3 fatty acid selected from ⁇ -linolenic acid (ALA) and stearidonic acid (SA) and from at least one polyphenol, as agent enhancing the endogenous synthesis of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), for the preparation of a dietary, dietetic or pharmaceutical composition for administration to a human or an animal.
  • omega-3 fatty acid selected from ⁇ -linolenic acid (ALA) and stearidonic acid (SA) and from at least one polyphenol, as agent enhancing the endogenous synthesis of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • the polyphenol may be chosen from apigenin, luteolin, chlorogenic acid, caffeic acid, ferulic acid, coumaric acids, hydroxycinnamic acid, acid salicylic acid, gallic acid, quercetin, eriodyctiol, catechin, epicatechin, epigallocatechin gallate, isorhamnetin, kaempherol, hesperetin, naringenin, phloretin, enterolactone, enterodiol , oleuropein, hydroxytyrosol, resveratrol, myricetin, rutin, phenolic acids, stilbenes, flavonoids and lignans.
  • the polyphenol is an anthocyanin.
  • the anthocyanin is chosen from cyanidine, delphidine, malvidine, peonidine, pelargonidine and petunidine.
  • the composition further comprises a compound selected from vitamins, mineral salts and trace elements.
  • the composition is in the form of granules, powder, liquid, semi-liquid.
  • the composition when it is a food or dietetic composition, it may be an oil, a margarine, a yogurt, a cheese, a bread, a rusk, a cake, a biscuit, a meal replacement, a cream, a chocolate bar, a cereal bar, or a compote made from fruit.
  • dietary or dietetic composition means any type of product intended to be ingested by the animal organism, in particular human.
  • dietary supplements are products intended to be ingested, in addition to the current diet, in order to compensate for the insufficiency of daily intake of certain compounds.
  • the food or dietetic composition of the invention can be in the form of granules, of powder, in liquid form in a natural way or be suspended or dissolved. It can be in a form adapted to the addition to the diet of an animal, or any other product constituting a food intake.
  • the composition according to the invention can be in dry, pasty, semi-pasty, liquid or semi-liquid form. These include, for example, food products, beverages, dietary supplements and nutraceuticals.
  • oils margarines and other fats, yoghurts, cheeses, including especially fresh cheeses and derived products, fermented products, products of the present invention.
  • dairy products, bread, rusks, and other cereal or derived products (pasta for example), cakes and cookies, meal replacements, snack foods in general, foods for children, babies and infants, creams, desserts, ice creams, chocolate bars, cereal bars, fruit compotes.
  • the composition is in a form suitable for adding an animal to the feed ration.
  • animal is meant more particularly, in addition to humans, livestock and especially grazing animals (including cattle raised for meat, milk and other dairy products, cheese and leather, sheep raised for meat, wool and cheese; goats; pigs), rabbits, poultry (chickens, chickens, turkeys, ducks, geese and others) reared for meat and meat products including eggs, aquatic animals (eg farm animals, fish, shrimps, oysters and mussels), recreational and companion animals (including horses, dogs, cats, pet birds, aquarium fish), laboratory animals (especially rats and mouse).
  • livestock and especially grazing animals including cattle raised for meat, milk and other dairy products, cheese and leather, sheep raised for meat, wool and cheese; goats; pigs
  • poultry chickens, chickens, turkeys, ducks, geese and others
  • recreational and companion animals including horses, dogs, cats, pet birds, aquarium fish
  • laboratory animals especially rats and mouse
  • compositions in particular but not exclusively, the compositions in solid, liquid, pasty semi-pasty, semi-liquid form.
  • a pharmaceutically acceptable excipient This is chosen so as to be suitable for the formulation of the two compounds of the composition (fatty acid and polyphenol).
  • the excipient is adapted to the desired route of administration and the nature of the desired dosage form.
  • the pharmaceutical compositions of the invention are available in all galenic forms suitable for administration. Said galenic forms may especially consist of: tablets, capsules, powders, granules, lyophilisates, drinkable solutions, syrups, suspensions and suppositories. This list is not exhaustive.
  • tablette refers to all kinds of tablets including effervescent tablets, dispersible tablets and orodispersible tablets.
  • composition of the invention when in the form of a granule or tablet, it may be in the form of a coating, so as to avoid the enzymatic destruction which takes place at a certain pH, and at the same time so as to allow the release controlled the active compound in another part of the digestive tract.
  • the composition according to the invention may also be in the form of sustained release or controlled release tablets.
  • omega-3 fatty acid polyunsaturated fatty acid, that is to say having at least one double bond, and whose first double bond connects the carbon atoms 3 and 4.
  • the fatty acid may have 3, 4 or 5 double bonds.
  • the fatty acid of the omega-3 group can have 18, 20, 22 or 24 carbon atoms.
  • the fatty acid of the omega-3 group may be an ⁇ -linolenic acid (ALA; C18: 3), a stearidonic acid (SA; C 1 8: 4), an eicosatetraenoic acid (ETA; C20: 4) , an eicosapentaenoic acid (EPA; C20: 5), an acid docosapentaenoic acid (DPA; C22: 5) or a mixture of at least two of these compounds.
  • ALA ⁇ -linolenic acid
  • SA stearidonic acid
  • ETA eicosatetraenoic acid
  • EPA eicosapentaenoic acid
  • DPA acid docosapentaenoic acid
  • the fatty acid of the omega-3 group is ⁇ -linolenic acid (ALA; C 1 8: 3) or stearidonic acid (SA; C18: 4).
  • Polyphenols are a family of organic molecules characterized by the presence of several phenolic groups. Their structure is more or less complex.
  • the polyphenols are chosen from those generally present in so-called Mediterranean foods, for example grapes, wine, citrus fruits, whole grains, legumes (in particular lentils, peas, beans), teas, coffee , olive oil, olives, linseed, linseed oil, walnuts, walnut oil, fruits (including cherry, plum, raspberry, blueberries, strawberries, currants, blackberries, cranberries ) and vegetables (including cucumbers, celery, zucchini, crucifers, including broccoli, artichoke, garlic, eggplant, tomatoes, red onions, peppers, carrots), and herbs (including thyme, basil, parsley, coriander, oregano, rosemary, chives, sage).
  • the polyphenols are also chosen from those generally present in foods containing fats, for example the polyphenols of cocoa, rapeseed, or aztec maize.
  • the polyphenols are chosen from apigenin, luteolin, chlorogenic acid, caffeic acid, ferulic acid, coumaric acids, hydroxycinnamic acid, and acid.
  • the polyphenols are chosen from phenolic acids, stilbenes, flavonoids and lignans.
  • the polyphenols are flavonoids, they are selected from anthocyanins and proanthocyanidins, flavonols, flavones, flavanones, flavanols, isoflavones and chalcones.
  • anthocyanins are cyanidin, delphidine, malvidine, peonidine, pelargonidine and petunidine.
  • the composition further comprises a compound selected from vitamins, mineral salts and trace elements.
  • Vitamins include vitamin C (ascorbic acid), vitamin B3 (nicotinamide), vitamin B5 (pantothenic acid), vitamin B6 (pyridoxine), vitamin B2 (riboflavin), vitamin B1 (thiamine) , vitamin B9 (folic acid), vitamin B8 (biotin), vitamin B12 (cyanocobalamin), vitamin D (calciferol), vitamin E (tocopherol), vitamin A (retinol) and vitamin K.
  • mineral salts mention may be made of calcium (Ca), iron (Fe), magnesium (Mg), sodium (Na), phosphorus (P), potassium (K) and sulfur (S).
  • trace elements mention may be made of aluminum (Al), arsenic (As), boron (B), chlorine (Cl), chromium (Cr), cobalt (Co), copper ( Cu), fluorine (F), iodine (I), manganese (Mn), molybdenum (Mo), nickel (Ni), lead (Pb), silicon (Si), selenium (Se) ), vanadium (V) and zinc (Zn).
  • compositions of the present invention are prepared by mixing said compounds.
  • the dietary or pharmaceutical food composition comprises a) from 1 to 99% by weight of at least one omega-3 fatty acid selected from ⁇ -linolenic acid and stearidonic acid; and b) from 99 to 1% by weight of said at least one polyphenol.
  • said at least one omega-3 fatty acid selected from ⁇ -linolenic acid and stearidonic acid is present between 10 and 90%, preferably between 20 and 80% and more preferably between 30 and 80%. and 70% by weight of the total weight of the composition.
  • said at least one polyphenol is present between 10 and 90%, preferably between 20 and 80% and more preferably between 30 and 70% by weight of the total weight of the composition.
  • the foods are prepared according to the protocol described in Tou Stammsian et al. (J Nutr 2008; 38: 747-752). Each diet is equivalent in energy terms with 67% of carbohydrates, 23% of proteins and 10% of lipids.
  • the fatty acid composition of each diet is given in Table 1.
  • the anthocyanins used in this test are derived from a non-genetically transformed corn so as to render it rich in anthocyanins.
  • the feed ration of the rats contains 20% processed corn, this percentage being relative to the total weight of maize present in the feed (in the form of pellets).
  • PUFA polyunsaturated fatty acids
  • triglyceride and cholesterol levels are not significantly affected by anthocyanin consumption.
  • the plasma levels of oleic, myristic and palmitic fatty acids are similar to those of rats not supplemented with polyphenol (ACN-free).
  • SFA, MUFA, PUFA and n-6 (or omega-6) levels are similar in both groups.
  • the levels in n-3 (or omega-3) and the ratio n-3: n-6 are nevertheless significantly increased after consumption of polyphenol (ACN-rich). In this respect, EPA and DHA levels are increased by 41% and 16% respectively.
  • n-3 and n-6 levels are not significantly different.
  • n-3: n-6 ratio increases significantly in animals receiving the combination of Palm Oil + anthocyanin.
  • EPA and DHA levels are increased by 25% and 10% respectively.
  • n-6 ratios were increased in animals receiving the EPA + DHA + anthocyanin combination.
  • EPA on the one hand
  • DHA on the other, are increased by 24% and 16%, respectively.
  • Palmitic 16 0 21.94 ⁇ 0.65 20.57 ⁇ 0.68
  • LA Linoleic
  • ALA ⁇ -linolenic
  • PUFA polyunsaturated fatty acids
  • Palmitic 16 0 22.65 ⁇ 0.27 22.96 ⁇ 0.56
  • PUFA polyunsaturated fatty acids
  • Palmitic 16 0 22.39 ' ⁇ 0.26 21.91 ⁇ 0.73
  • Olieic 18 ln-9 9.35 ⁇ 0.34 10.07 ⁇ 0.44
  • LA Linoleic
  • ALA ⁇ -linolenic
  • PUFA polyunsaturated fatty acids

Abstract

The present invention relates to the use of at least one fatty acid of the omega-3 group, selected from among α-linolenic acid and stearidonic acid, and of at least one polyphenol as an agent for increasing the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid, for preparing a food, health, or pharmaceutical composition to be administered to a human being or to an animal.

Description

Utilisation d'au moins un acide gras oméga-3 et d'au moins un polyphénol pour la synthèse endogène d'acide éicosapentaénoïque et d'acide docosahexaénoïque La présente invention concerne, de manière générale, l 'al i m entation a n i ma l e , nota m m ent h u m a i n e, et en particu l i er l a complémentation de cette alimentation avec une composition contenant un mélange d'au moins un acide gras oméga-3 avec un polyphénol destiné à augmenter la synthèse endogène d'acides gras oméga-3 à 20 ou 22 atomes de carbone (appelés acides gras oméga-3 à très longues chaînes ou TLC).  The present invention relates, in general, to the use of at least one omega-3 fatty acid and at least one polyphenol for the endogenous synthesis of eicosapentaenoic acid and docosahexaenoic acid. human body, and in particular supplementing this diet with a composition containing a mixture of at least one omega-3 fatty acid with a polyphenol for increasing the endogenous synthesis of omega-3 fatty acids at 20 or 22 carbon atoms (termed very long chain omega-3 fatty acids or TLC).
Les principaux acides gras du groupe oméga-3 sont l'acide α- linolénique ou ω3α (18:3; ALA), l'acide éicosapentaénoïque (20:5; EPA) et l'acide docosahexaénoïque (22:6; DHA). Ils sont qualifiés d'acides gras essentiels car le corps animal, notamment humain, ne sait pas les synthétiser ou sait les synthétiser en quantité insuffisante. Un apport minimal et régulier par l'alimentation est considéré comme nécessaire par les experts.  The main omega-3 fatty acids are α-linolenic acid or ω3α (18: 3, ALA), eicosapentaenoic acid (20: 5, EPA) and docosahexaenoic acid (22: 6, DHA). They are called essential fatty acids because the animal body, especially human, does not know how to synthesize them or knows how to synthesize them in insufficient quantity. A minimal and regular intake of food is considered necessary by the experts.
O n t rouve des quantités importantes d'acides gras TLC, notamment EPA et DHA, dans le poisson gras. Les nutritionnistes recommandent donc une consommation de poisson régulière. Néanmoins, l'augmentation de la consommation de poissons dans le monde conduit à la surpêche et la désertification des mers. Une alternative à la surpêche réside dans l'existence de poisson d'élevage dans les fermes marines. Le plancton qui renferme des quantités importantes de DHA et d'EPA est indispensable à l'alimentation des poissons d'élevage. Le plancton est collecté par les bateaux moissonneurs, ce qu i conduit à l'appauvrissement des mers. Cette chaîne d'événements conduit à u n bouleversement écologique et à des conflits violents avec l'industrie du poisson.  Large amounts of TLC fatty acids, including EPA and DHA, are found in oily fish. Nutritionists therefore recommend regular fish consumption. Nevertheless, the increase in fish consumption around the world is leading to overfishing and the desertification of the seas. An alternative to overfishing is the existence of farmed fish on marine farms. Plankton containing significant amounts of DHA and EPA is essential for feeding farmed fish. The plankton is collected by the harvesters, which leads to the impoverishment of the seas. This chain of events is leading to ecological upheaval and violent conflict with the fish industry.
On trouve de l'ALA dans les plantes, mais cet ALA n'est pas transformé de façon efficace en TLC par les animaux, notamment les humains. L'utilisation d'ALA ne peut donc pas, selon les experts suppléer un déficit d'apport en oméga-3 TLC d'origine marine.  ALA is found in plants, but ALA is not efficiently transformed into TLC by animals, especially humans. The use of ALA can not therefore, according to experts provide a lack of intake of omega-3 TLC of marine origin.
La présente invention propose une solution de remplacement à la consommation alimentaire d'acides gras TLC d'origine essentiellement marine.  The present invention provides an alternative to the dietary consumption of TLC fatty acids of essentially marine origin.
Les inventeurs se sont rendu compte que l'apport simultané d'ALA et de polyphénols conduisait à une augmentation de la synthèse endogène d'acides gras TLC, notamment EPA et DHA. II est à noter qu'un certains nombre d'articles scientifiques font état de l'effet positif de la consommation de vin sur la concentration plasmatique de TLC. Notamment l'article de De Lorgeril et al., (American Heart Journal, 2008, 155:175-181 ) étudie l'effet du vin sur le métabolisme des oméga-3 et conclut qu'une augmentation de la consommation d'ALA associée à une consommation modérée d'éthanol re p rése n te u n e a l te rn at i ve à la consommation de poisson. Egalement, l'article de Guiraud et al. (British Journal of Nutrition 2008, 100, 1237-1244) étudie l'effet de l'éthanol sur le métabolisme des acides gras essentiels chez le rat. L'article de Di Giuseppe et al. (Am J Clin Nutr 2009, 89 :1 -9) étudie les concentrations d'acides gras oméga-3 chez les consommateurs de vin par comparaison aux non buveurs et aux buveurs d'autres boissons alcooliques et conclut que des composants du vin autres que l'éthanol pourraient avoir un effet sur la concentration plasmatique d'acides gras oméga-3. The inventors have realized that the simultaneous supply of ALA and polyphenols led to an increase in the endogenous synthesis of TLC fatty acids, in particular EPA and DHA. It should be noted that a number of scientific articles report the positive effect of wine consumption on the plasma concentration of TLC. Notably the article by De Lorgeril et al., (American Heart Journal, 2008, 155: 175-181) studies the effect of wine on the metabolism of omega-3 and concludes that an increase in ALA consumption associated at a moderate consumption of ethanol is uniquely rese ted to fish consumption. Also, the article by Guiraud et al. (British Journal of Nutrition 2008, 100, 1237-1244) studies the effect of ethanol on the metabolism of essential fatty acids in rats. The article by Di Giuseppe et al. (Am J Clin Nutr 2009, 89: 1-9) studies omega-3 fatty acid levels in wine consumers compared to non-drinkers and drinkers of other alcoholic beverages and concludes that wine components other than ethanol may affect the plasma concentration of omega-3 fatty acids.
La présente invention concerne l'utilisation d'au moins un acide gras du groupe oméga-3 choisi parmi l'acide α-linolénique (ALA) et l'acide stéaridonique (SA) et d'au moins un polyphénol, en tant qu'agent augmentant la synthèse endogène d'acide éicosapentaénoïque (EPA) et d'acide docosahexaénoïque (DHA), pour la préparation d'une composition alimentaire, diététique ou pharmaceutique destinée à être administrée à un être humain ou à un animal.  The present invention relates to the use of at least one omega-3 fatty acid selected from α-linolenic acid (ALA) and stearidonic acid (SA) and from at least one polyphenol, as agent enhancing the endogenous synthesis of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), for the preparation of a dietary, dietetic or pharmaceutical composition for administration to a human or an animal.
Dans un mode de réalisation de l'invention, le polyphénol peut être choisi parmi l'apigénine, la lutéoline, l'acide chlorogénique, l'acide caféique, l'acide férulique, les acides coumariques, l'acide hydroxycinnamique, l'acide salicylique, l'acide gallique, la quercétine, l'eriodyctiol, la catéchine, l'épicatéchine, l'epigallocatéchine gallate, l'isorhamnétine, le kaempherol, l'hesperétine, la naringénine, la phlorétine, l'entérolactone, l'entérodiol, l'oleuropéine, l'hydroxytyrosol, le resvératrol, la myricétine, la rutine, les acides phénoliques, les stilbènes, les flavonoïdes et les lignanes.  In one embodiment of the invention, the polyphenol may be chosen from apigenin, luteolin, chlorogenic acid, caffeic acid, ferulic acid, coumaric acids, hydroxycinnamic acid, acid salicylic acid, gallic acid, quercetin, eriodyctiol, catechin, epicatechin, epigallocatechin gallate, isorhamnetin, kaempherol, hesperetin, naringenin, phloretin, enterolactone, enterodiol , oleuropein, hydroxytyrosol, resveratrol, myricetin, rutin, phenolic acids, stilbenes, flavonoids and lignans.
De manière préférée, le polyphénol est une anthocyanine. Preferably, the polyphenol is an anthocyanin.
De manière tout à fait avantageuse, l'anthocyanine est choisie parmi la cyanidine, la delphidine, la malvidine, la peonidine, la pélargonidine et la pétunidine. In a most advantageous manner, the anthocyanin is chosen from cyanidine, delphidine, malvidine, peonidine, pelargonidine and petunidine.
Dans un mode de réal isation de l'invention , la composition comprend en outre un composé choisi parmi les vitamines, les sels minéraux et les oligo-éléments. Avantageusement, la composition se trouve sous la forme de granules, de poudre, de liquide, de semi-liquide. In one embodiment of the invention, the composition further comprises a compound selected from vitamins, mineral salts and trace elements. Advantageously, the composition is in the form of granules, powder, liquid, semi-liquid.
De manière préférée, lorsque la composition est une composition alimentaire ou diététique, il peut s'agir d'une huile, d'une margarine, d'un yaourt, d'un fromage, d'un pain, d'une biscotte, d'un gâteau, d'un biscuit, d'un substitut de repas, d'une crème, d'une barre chocolatée, d'une barre de céréales, ou encore d'une compote à base de fruits.  Preferably, when the composition is a food or dietetic composition, it may be an oil, a margarine, a yogurt, a cheese, a bread, a rusk, a cake, a biscuit, a meal replacement, a cream, a chocolate bar, a cereal bar, or a compote made from fruit.
Au sens de la présente invention, on entend par « composition alimentaire ou diététique » tout type de produit destiné à être ingéré par l'organisme animal, notamment humain. Entrent notamment dans le champ de protection de la présente invention les compléments alimentaires. Les compléments alimentaires sont des produits destinés à être ingérés, en complément de l'alimentation courante, afin de pallier l'insuffisance des apports journaliers en certains composés. La composition alimentaire ou diététique de l'invention peut se trouver sous forme de granules, de poudre, sous forme liquide de façon naturelle ou être mise en suspension ou mise en solution. Elle peut se présenter sous forme adaptée à l'ajout à la ration alimentaire d'un animal, ou à tout autre produit constituant un apport alimentaire. A ce titre la composition selon l'invention peut se trouver sous forme sèche, pâteuse, semi- pâteuse, liquide ou semi-liquide. Il s'agit par exemple de produits alimentaires, de boissons, de suppléments alimentaires et de produits nutraceutiques.  For the purposes of the present invention, the term "dietary or dietetic composition" means any type of product intended to be ingested by the animal organism, in particular human. Particularly within the scope of the present invention are dietary supplements. Food supplements are products intended to be ingested, in addition to the current diet, in order to compensate for the insufficiency of daily intake of certain compounds. The food or dietetic composition of the invention can be in the form of granules, of powder, in liquid form in a natural way or be suspended or dissolved. It can be in a form adapted to the addition to the diet of an animal, or any other product constituting a food intake. As such, the composition according to the invention can be in dry, pasty, semi-pasty, liquid or semi-liquid form. These include, for example, food products, beverages, dietary supplements and nutraceuticals.
Parmi les produits alimentaires destinés aux êtres humains plus particulièrement concernés par la présente invention, on peut citer les huiles, margarines et autres matières grasses, les yaourts, les fromages, dont notamment les fromages frais et les produits dérivés, les produits fermentes, les produits laitiers, le pain, les biscottes, et autres produits céréaliers ou dérivés (les pâtes par exemples), les gâteaux et biscuits, les substituts de repas, les produits de grignotage en général, les aliments destinés aux enfants, aux bébés et aux nourrissons, les crèmes, les entremets, les crèmes glacées, les barres chocolatées, les barres de céréales, les compotes à base de fruits.  Among the food products intended for humans that are more particularly concerned by the present invention, mention may be made of oils, margarines and other fats, yoghurts, cheeses, including especially fresh cheeses and derived products, fermented products, products of the present invention. dairy products, bread, rusks, and other cereal or derived products (pasta for example), cakes and cookies, meal replacements, snack foods in general, foods for children, babies and infants, creams, desserts, ice creams, chocolate bars, cereal bars, fruit compotes.
Selon un mode de réalisation et conformément à la présente invention, la composition se trouve sous forme adaptée à l'ajout à la ration alimentaire d'un animal. Par "animal", on entend plus particulièrement, outre les humains, les animaux d'élevage et notamment les animaux de pacage (notamment les bovins élevés pour la viande, le lait et autres produits laitiers, le fromage et le cuir ; les ovins élevés pour la viande, la laine et le fromage ; les caprins ; les porcins), les lapins, les volailles (les poulets, les poules, les dindes, les canards, les oies et autres) élevés pour leurs viandes et produits dérivés dont les œufs, les animaux aquatiques (par exemple les animaux des fermes marines, les poissons, les crevettes, les huîtres et les moules), les animaux de loisir et de compagnie (notamment le cheval, le chien, le chat, les oiseaux de compagnie, les poissons d'aquarium), les animaux de laboratoire (notamment rats et souris). According to one embodiment and in accordance with the present invention, the composition is in a form suitable for adding an animal to the feed ration. By "animal" is meant more particularly, in addition to humans, livestock and especially grazing animals (including cattle raised for meat, milk and other dairy products, cheese and leather, sheep raised for meat, wool and cheese; goats; pigs), rabbits, poultry (chickens, chickens, turkeys, ducks, geese and others) reared for meat and meat products including eggs, aquatic animals (eg farm animals, fish, shrimps, oysters and mussels), recreational and companion animals (including horses, dogs, cats, pet birds, aquarium fish), laboratory animals (especially rats and mouse).
Par « composition pharmaceutique », on entend notamment mais non exclusivement, les compositions sous forme solide, liquide, pâteuse semi- pâteuse, semi-liquide. Lorsque la présente invention concerne une composition pharmaceutique, elle contient un excipient pharmaceutiquement acceptable. Celui-ci est choisi de manière à convenir à la formulation des deux composés de la composition (acide gras et polyphénol). L'excipient est adapté à la voie d'administration souhaitée et à la nature de la forme galénique souhaitée. Les compositions pharmaceutiques de l'invention se déclinent sous toutes formes galéniques convenant à l'administration. Lesdites formes galéniques peuvent notamment consister en : des comprimés, des gélules, des poudres, des granulés, des lyophilisats, des solutés buvables, des sirops, des suspensions et des suppositoires. Cette liste n'est pas exhaustive. Le terme "comprimé" désigne toutes sortes de comprimés et notamment les comprimés effervescents, les comprimés dispersibles et les comprimés orodispersibles.  By "pharmaceutical composition" is meant in particular but not exclusively, the compositions in solid, liquid, pasty semi-pasty, semi-liquid form. When the present invention relates to a pharmaceutical composition, it contains a pharmaceutically acceptable excipient. This is chosen so as to be suitable for the formulation of the two compounds of the composition (fatty acid and polyphenol). The excipient is adapted to the desired route of administration and the nature of the desired dosage form. The pharmaceutical compositions of the invention are available in all galenic forms suitable for administration. Said galenic forms may especially consist of: tablets, capsules, powders, granules, lyophilisates, drinkable solutions, syrups, suspensions and suppositories. This list is not exhaustive. The term "tablet" refers to all kinds of tablets including effervescent tablets, dispersible tablets and orodispersible tablets.
Lorsque la composition de l'invention se trouve sous forme de granule ou de comprimé, elle peut se trouver sous forme enrobée, de manière à éviter la destruction enzymatique qui a lieu à un certain pH, et en même temps de manière à permettre la libération contrôlée du composé actif dans une autre partie de l'appareil digestif. La composition selon l'invention peut également se trouver sous forme de comprimés à libération prolongée ou à libération contrôlée.  When the composition of the invention is in the form of a granule or tablet, it may be in the form of a coating, so as to avoid the enzymatic destruction which takes place at a certain pH, and at the same time so as to allow the release controlled the active compound in another part of the digestive tract. The composition according to the invention may also be in the form of sustained release or controlled release tablets.
Par « acide gras du groupe oméga-3 », on entend acide gras polyinsaturés, c'est-à-dire présentant au moins une double liaison, et dont la première double liaison relie les atomes de carbone 3 et 4. A titre indicatif, l'acide gras peut comporter 3, 4 ou 5 doubles liaisons. L'acide gras du groupe oméga-3 peut comporter 18, 20, 22 ou 24 atomes de carbone. Par exemple, l'acide gras du groupe oméga-3 peut être un acide α-linolénique (ALA ; C18:3), un acide stéaridonique (SA ; C 1 8:4), un acide eicosatétraénoïque (ETA ; C20:4), un acide eicosapentaénoïque (EPA ; C20:5), un acide docosapentaénoïque (DPA ; C22:5) ou un mélange d'au moins deux de ces composés. By "omega-3 fatty acid" is meant polyunsaturated fatty acid, that is to say having at least one double bond, and whose first double bond connects the carbon atoms 3 and 4. As an indication, the fatty acid may have 3, 4 or 5 double bonds. The fatty acid of the omega-3 group can have 18, 20, 22 or 24 carbon atoms. For example, the fatty acid of the omega-3 group may be an α-linolenic acid (ALA; C18: 3), a stearidonic acid (SA; C 1 8: 4), an eicosatetraenoic acid (ETA; C20: 4) , an eicosapentaenoic acid (EPA; C20: 5), an acid docosapentaenoic acid (DPA; C22: 5) or a mixture of at least two of these compounds.
Selon un mode de réalisation de la présente invention, l'acide gras du groupe oméga-3 est l'acide α-linolénique (ALA ; C 1 8:3) ou l'acide stéaridonique (SA ; C18:4).  According to one embodiment of the present invention, the fatty acid of the omega-3 group is α-linolenic acid (ALA; C 1 8: 3) or stearidonic acid (SA; C18: 4).
Les polyphénols constituent une famille de molécules organiques caractérisées par la présence de plusieurs groupements phénoliques. Leur structure est plus ou moins complexes.  Polyphenols are a family of organic molecules characterized by the presence of several phenolic groups. Their structure is more or less complex.
Selon la présente invention, les polyphénols sont choisis parmi ceux généralement présents dans des aliments dits méditerranéens, par exemple le raisin, le vin, les agrumes, les céréales complètes, les légumineuses (notamment lentilles, pois, fèves), les thés, le café, l'huile d'olive, les olives, les graines de lin, l'huile de lin, les noix, l'huile de noix, les fruits (notamment cerise, prune, framboise, myrtilles, fraises, groseilles, mûres, cranberries) et les légumes (notamment concombres, céleri, courgette, crucifères dont brocoli, artichaut, ail, aubergine, tomates, oignons rouges, poivron, carotte), et les herbes aromatiques (notamment thym, basilic, persil, coriandre, origan, romarin, ciboulette, sauge). Selon la présente invention, les polyphénols sont également choisis parmi ceux généralement présents dans des aliments contenant des matières grasses, par exemple les polyphénols du cacao, du colza, du maïs aztèque.  According to the present invention, the polyphenols are chosen from those generally present in so-called Mediterranean foods, for example grapes, wine, citrus fruits, whole grains, legumes (in particular lentils, peas, beans), teas, coffee , olive oil, olives, linseed, linseed oil, walnuts, walnut oil, fruits (including cherry, plum, raspberry, blueberries, strawberries, currants, blackberries, cranberries ) and vegetables (including cucumbers, celery, zucchini, crucifers, including broccoli, artichoke, garlic, eggplant, tomatoes, red onions, peppers, carrots), and herbs (including thyme, basil, parsley, coriander, oregano, rosemary, chives, sage). According to the present invention, the polyphenols are also chosen from those generally present in foods containing fats, for example the polyphenols of cocoa, rapeseed, or aztec maize.
Selon un mode de réal isation de la présente invention, les polyphénols sont choisis parmi l'apigénine, la lutéoline, l'acide chlorogénique, l'acide caféique, l'acide férulique, les acides coumariques, l'acide hydroxycinnamique, l'acide salicylique, l'acide gallique, la quercétine, l'eriodyctiol, la catéchine, l'épicatéchine, l'epigallocatéchine gallate, l'isorhamnétine, le kaempherol, l'hesperétine, la naringénine, la phlorétine, l'entérolactone, l'entérodiol, l'oleuropéine, l'hydroxytyrosol, le resvératrol, la myricétine et la rutine.  According to one embodiment of the present invention, the polyphenols are chosen from apigenin, luteolin, chlorogenic acid, caffeic acid, ferulic acid, coumaric acids, hydroxycinnamic acid, and acid. salicylic acid, gallic acid, quercetin, eriodyctiol, catechin, epicatechin, epigallocatechin gallate, isorhamnetin, kaempherol, hesperetin, naringenin, phloretin, enterolactone, enterodiol , oleuropein, hydroxytyrosol, resveratrol, myricetin and rutin.
Selon un autre mode de réalisation de la présente invention, les polyphénols sont choisis parmi les acides phénoliques, les stilbènes, les flavonoïdes et les lignanes. Lorsque les polyphénols sont des flavonoïdes, ils sont choisis parmi les anthocyanines et les proanthocyanidines, les flavonols, les flavones, les flavanones, les flavanols, les isoflavones et les chalcones. Des exemples d'anthocyanines sont la cyanidine, la delphidine, la malvidine, la peonidine, la pélargonidine et la pétunidine. Selon un mode de réalisation de la présente invention, la composition comprend, en outre, un composé choisi parmi les vitamines, les sels minéraux et les oligo-éléments. According to another embodiment of the present invention, the polyphenols are chosen from phenolic acids, stilbenes, flavonoids and lignans. When the polyphenols are flavonoids, they are selected from anthocyanins and proanthocyanidins, flavonols, flavones, flavanones, flavanols, isoflavones and chalcones. Examples of anthocyanins are cyanidin, delphidine, malvidine, peonidine, pelargonidine and petunidine. According to one embodiment of the present invention, the composition further comprises a compound selected from vitamins, mineral salts and trace elements.
Parmi les vitamines, on peut citer la vitamine C (acide ascorbique), la vitamine B3 (nicotinamide), la vitamine B5 (acide pantothénique), la vitamine B6 (pyridoxine), la vitamine B2 (riboflavine), l a vitamine B1 (thiamine), la vitamine B9 (acide folique), la vitamine B8 (biotine), la vitamine B12 (cyanocobalamine), la vitamine D (calciférol), la vitamine E( tocophérol), la vitamine A (rétinol) et la vitamine K.  Vitamins include vitamin C (ascorbic acid), vitamin B3 (nicotinamide), vitamin B5 (pantothenic acid), vitamin B6 (pyridoxine), vitamin B2 (riboflavin), vitamin B1 (thiamine) , vitamin B9 (folic acid), vitamin B8 (biotin), vitamin B12 (cyanocobalamin), vitamin D (calciferol), vitamin E (tocopherol), vitamin A (retinol) and vitamin K.
Parmi les sels minéraux, on peut citer le calcium (Ca), le fer (Fe), le magnésium (Mg), le sodium (Na), le phosphore (P), le potassium (K), le soufre (S).  Among the mineral salts, mention may be made of calcium (Ca), iron (Fe), magnesium (Mg), sodium (Na), phosphorus (P), potassium (K) and sulfur (S).
Parmi les oligo-éléments, on peut citer l'aluminium (Al), l'arsenic (As), le bore (B), le chlore (Cl), le chrome (Cr), le cobalt (Co), le cuivre (Cu), le fluor (F), l'iode (I), le manganèse (Mn), le molybdène (Mo), le nickel (Ni), le plomb (Pb), le silicium (Si), le sélénium (Se), le vanadium (V) et le zinc (Zn).  Among the trace elements, mention may be made of aluminum (Al), arsenic (As), boron (B), chlorine (Cl), chromium (Cr), cobalt (Co), copper ( Cu), fluorine (F), iodine (I), manganese (Mn), molybdenum (Mo), nickel (Ni), lead (Pb), silicon (Si), selenium (Se) ), vanadium (V) and zinc (Zn).
Les compositions de la présente invention sont préparées par mélange desdits composés.  The compositions of the present invention are prepared by mixing said compounds.
La composition alimentaire, diététique ou pharmaceutique, comprend a) de 1 à 99% en poids d'au moins un acide gras du groupe oméga- 3 choisi parmi l'acide α-linolénique et l'acide stéaridonique; et b) de 99 à 1 % en poids dudit au moins un polyphénol.  The dietary or pharmaceutical food composition comprises a) from 1 to 99% by weight of at least one omega-3 fatty acid selected from α-linolenic acid and stearidonic acid; and b) from 99 to 1% by weight of said at least one polyphenol.
Selon un autre mode de réalisation, ledit au moins un acide gras du groupe oméga-3 choisi parmi l'acide α-linolénique et l'acide stéaridonique est présent entre 10 et 90%, préférentiellement entre 20 et 80% et mieux encore entre 30 et 70 % en poids du poids total de la composition.  According to another embodiment, said at least one omega-3 fatty acid selected from α-linolenic acid and stearidonic acid is present between 10 and 90%, preferably between 20 and 80% and more preferably between 30 and 80%. and 70% by weight of the total weight of the composition.
Selon un autre mode de réalisation, ledit au moins un polyphénol est présent entre 10 et 90%, préférentiellement entre 20 et 80% et mieux encore entre 30 et 70 % en poids du poids total de la composition. Exemple Matériel et méthodes According to another embodiment, said at least one polyphenol is present between 10 and 90%, preferably between 20 and 80% and more preferably between 30 and 70% by weight of the total weight of the composition. Example Material and methods
Les aliments sont préparés selon le protocole décrit dans Toufektsian et al. (J Nutr 2008 ; 1 38 : 747-752). Chaque régime est équivalent en terme énergétique avec 67% de carbohydrates, 23% de protéines et 10% de lipides. La composition en acides gras de chaque régime est donnée au Tableau 1. Les anthocyanines utilisés dans le présent essai proviennent d'un maïs transformé (de façon non génétique) de façon à le rendre riche en anthocyanines Dans le cas du régime riche en anthocyanines, la ration alimentaire des rats contient 20% de maïs transformé ce pourcentage étant relatif au poids total de maïs présent dans l'aliment (sous forme de pellets). The foods are prepared according to the protocol described in Toufektsian et al. (J Nutr 2008; 38: 747-752). Each diet is equivalent in energy terms with 67% of carbohydrates, 23% of proteins and 10% of lipids. The fatty acid composition of each diet is given in Table 1. The anthocyanins used in this test are derived from a non-genetically transformed corn so as to render it rich in anthocyanins. In the case of the anthocyanin-rich diet, the feed ration of the rats contains 20% processed corn, this percentage being relative to the total weight of maize present in the feed (in the form of pellets).
Figure imgf000009_0001
Figure imgf000009_0001
SFA : acides gras saturés  SFA: saturated fatty acids
PUFA : acides gras polyinsaturés PUFA: polyunsaturated fatty acids
MUFA : acides gras monoinsaturés Trois protocoles différents ont été suivis. MUFA: monounsaturated fatty acids Three different protocols were followed.
Protocole 1 : Protocol 1:
L'étude est menée sur 8 semaines. 31 animaux sont séparés en deux groupes expérimentaux. Les animaux du 1er groupe (n=15) sont nourris avec un régime de base, sans anthocyanine (ACN-free). Les animaux du deuxième groupe (n=16) sont nourris avec le même régime de base auquel on ajoute des anthocyanines (ACN-rich). Protocole 2 : The study is conducted over 8 weeks. 31 animals are separated into two experimental groups. Animals in the 1st group (n = 15) are fed a basic diet without anthocyanin (ACN-free). Animals in the second group (n = 16) are fed the same basic diet supplemented with anthocyanins (ACN-rich). Protocol 2:
L'étude est menée sur 8 semaines. 25 animaux sont séparés en deux groupes expérimentaux. Les animaux du 1 er groupe (n = 15) sont nourris avec un régime de base sans anthocyanine (ACN-free). Les animaux du deuxième groupe (n=10) sont nourris avec un régime de base avec anthocyanines (ACN-rich). Les animaux des deux groupes reçoivent en outre une adm in istration journal ière ora l e d ' h u i l e d e p a l m e ( 80 μ L/j ) . Cette complémentation apporte 37 mg/j de SFA, 28 mg/j de MUFA et 7 mg/j de PUFA. L'huile de palme ne contient ni ALA, ni EPA ni DHA. The study is conducted over 8 weeks. 25 animals are separated into two experimental groups. Animals in the 1st group (n = 15) are fed a basic diet without anthocyanin (ACN-free). Animals in the second group (n = 10) are fed a basic diet with anthocyanins (ACN-rich). The animals of the two groups also receive a daily adminstration ora huileepalme (80 μL / d). This supplementation provides 37 mg / day of SFA, 28 mg / day of MUFA and 7 mg / day of PUFA. Palm oil does not contain ALA, EPA or DHA.
Protocole 3 : Protocol 3:
L'étude est menée sur 8 semaines. 29 animaux sont séparés en deux groupes expérimentaux. Les animaux du 1 er groupe (n = 18) sont nourris avec un régime de base sans anthocyanine (ACN-free). Les animaux du deuxième groupe (n=1 1 ) sont nourris avec un régime de base avec anthocyanines (ACN-rich). Les animaux des deux groupes reçoivent en outre une administration journalière orale d'acides polyinsaturés (n-3 à longues chaînes : EPA et DHA à 60mg/j sous forme d'éthyl esters) ne contenant pas d'ALA. Dans les trois protocoles ci-dessus, la masse corporelle et la consommation de nourriture sont mesurées chaque semaine. A la fin de la période expérimentale (8 semaines), les animaux sont anesthésiés et héparinisés. Après excision du cœur, le sang est collecté dans le thorax. Le plasma est obtenu après centrifugation (5 minutes, 1000g, 4°C). Les échantillons sont conservés à 800C pour les analyses en acides gras subséquentes. The study is conducted over 8 weeks. 29 animals are separated into two experimental groups. Animals of group 1 (n = 18) were fed a basic diet without anthocyanin (ACN-free). Animals in the second group (n = 1 1) are fed a basic diet with anthocyanins (ACN-rich). The animals of the two groups also receive an oral daily administration of polyunsaturated acids (long-chain n-3: EPA and DHA at 60 mg / day in the form of ethyl esters) not containing ALA. In the three protocols above, body weight and food consumption are measured weekly. At the end of the experimental period (8 weeks), the animals are anesthetized and heparinized. After excision of the heart, the blood is collected in the thorax. Plasma is obtained after centrifugation (5 minutes, 1000g, 4 ° C). The samples are stored at 80 ° C. for subsequent fatty acid analyzes.
Résultats Results
Masse corporelle et consommation de nourriture Body mass and food consumption
Protocole 1 :  Protocol 1:
L'évolution de la masse corporelle est similaire chez les rats ACN-free et les rats ACN-rich. La consommation journalière de nourriture est équivalente dans les deux groupes (ACN-free: 22.0 ± 0.4 g vs. ACN-rich: 21.8 ± 0.3 g, P = NS).  The evolution of body mass is similar in ACN-free rats and ACN-rich rats. The daily consumption of food is equivalent in both groups (ACN-free: 22.0 ± 0.4 g vs. ACN-rich: 21.8 ± 0.3 g, P = NS).
Protocole 2 :  Protocol 2:
Chez les rats supplémentés en huile de palme, la masse corporelle et la prise de nourriture journalière (ACN-free + Huile Palme: 23.4 ± 0.8 g vs. ACN-rich + Huile Palme : 23.3 ± 1 .1 g, P = NS) ne sont pas significativement affectés par la consommation d'anthocyanines. In rats supplemented with palm oil, body mass and daily food intake (ACN-free + Palm Oil: 23.4 ± 0.8 g vs. ACN-rich + Palm oil: 23.3 ± 1.1 g, P = NS) are not significantly affected by anthocyanin consumption.
Protocole 3 :  Protocol 3:
De manière similaire, les anthocyanines alimentaires n'induisent de modifications ni dans la prise de poids, ni dans la consommation alimentaire journalière (ACN-free+n-3: 21.8 ± 0.6 g vs. ACN-rich+n-3: 22.0 ± 0.3 g, P = NS) chez les rats recevant en outre une supplémentation journalière orale d'acides polyinsaturés. Effet des anthocyanines sur le métabolisme des acides gras  Similarly, dietary anthocyanins induce no changes in weight gain or in daily dietary intake (ACN-free + n-3: 21.8 ± 0.6 g vs. ACN-rich + n-3: 22.0 ± 0.3 g, P = NS) in rats additionally receiving daily oral supplementation of polyunsaturated acids. Effect of anthocyanins on fatty acid metabolism
Voir les tableaux 2, 3 et 4 See Tables 2, 3 and 4
Protocole 1 : Protocol 1:
Tel que montré dans le tableau 2, les taux de triglycérides et de cholestérol ne sont pas significativement modifiés par la consommation d'anthocyanine. Chez les rats complémentés en polyphénol (ACN-rich), les taux plasmatiques d'acides gras oléique, myristique et palmitique sont similaires à ceux des rats non complémentés en polyphénol (ACN-free). Les taux de SFA, MUFA, PUFA et n-6 (ou oméga-6) sont similaires dans les deux groupes. Les taux en n-3 (ou oméga-3) et le ratio n-3:n-6 sont néanmoins significativement augmentés après consommation de polyphénol (ACN-rich). A cet égard, les taux d'EPA et de DHA sont augmentés respectivement de 41 % et 16%. As shown in Table 2, triglyceride and cholesterol levels are not significantly affected by anthocyanin consumption. In rats supplemented with polyphenol (ACN-rich), the plasma levels of oleic, myristic and palmitic fatty acids are similar to those of rats not supplemented with polyphenol (ACN-free). SFA, MUFA, PUFA and n-6 (or omega-6) levels are similar in both groups. The levels in n-3 (or omega-3) and the ratio n-3: n-6 are nevertheless significantly increased after consumption of polyphenol (ACN-rich). In this respect, EPA and DHA levels are increased by 41% and 16% respectively.
Protocole 2 :  Protocol 2:
Tel que montré dans le tableau 3, les taux de SFA, MUFA et PUFA sont comparables dans les deux groupes. Les taux n-3 et n-6 ne sont pas significativement différents. Cependant le ratio n-3:n-6 augmente de manière significative chez les animaux recevant conjointement la combinaison Huile de Palme + anthocyan ines. A cet égard , les taux d'EPA et de DHA sont augmentés respectivement de 25% et 10%. As shown in Table 3, the SFA, MUFA and PUFA levels are comparable in both groups. The n-3 and n-6 levels are not significantly different. However, the n-3: n-6 ratio increases significantly in animals receiving the combination of Palm Oil + anthocyanin. In this respect, EPA and DHA levels are increased by 25% and 10% respectively.
Protocole 3 :  Protocol 3:
Tel que montré dans le tableau 4, les taux plasmatiques de SFA, MUFA, PUFA et n-6 sont similaires dans les deux groupes. Par contre, les taux de n-3 et le ratio n-3:n-6 sont augmentés chez les animaux recevant conjointement la combinaison EPA + DHA + anthocyanines. A cet égard, les taux d'EPA, d'une part, et de DHA, d'autre part, sont augmentés de respectivement 24% et 16%. ACN-free ACN-rich As shown in Table 4, the plasma levels of SFA, MUFA, PUFA and n-6 are similar in both groups. In contrast, n-3 and n-3: n-6 ratios were increased in animals receiving the EPA + DHA + anthocyanin combination. In this respect, EPA, on the one hand, and DHA, on the other, are increased by 24% and 16%, respectively. ACN-free ACN-rich
(n = 15) (n = 16)  (n = 15) (n = 16)
Lipides du sang (g/L) Blood lipids (g / L)
Total Cholestérol 0.41 ±0.07 0.50 ±0.02  Total Cholesterol 0.41 ± 0.07 0.50 ± 0.02
HDL Cholestérol 0.37 ±0.02 0.39 ±0.02  HDL Cholesterol 0.37 ± 0.02 0.39 ± 0.02
Acides gras (% des acides gras totaux) Fatty acids (% of total fatty acids)
Myristique 14 :0 0.77 ±0.07 0.72 ±0.08 Myristic 14: 0 0.77 ± 0.07 0.72 ± 0.08
Palmitique 16 :0 21.94 ±0.65 20.57 ±0.68Palmitic 16: 0 21.94 ± 0.65 20.57 ± 0.68
Stéarique 18 :0 6.30 ±0.39 6.02 ±0.37Stearic 18: 0 6.30 ± 0.39 6.02 ± 0.37
Oléique 18 :ln-9 12.84 ±0.74 11.93 ± 1.13Oleic 18: ln-9 12.84 ± 0.74 11.93 ± 1.13
Linoléique (LA) 18 :2n-6 23.41 ±0.92 23.81 ±0.51 α-linolénique (ALA) 18 :3n-3 0.75 ±0.08 0.76 ±0.07Linoleic (LA) 18: 2n-6 23.41 ± 0.92 23.81 ± 0.51 α-linolenic (ALA) 18: 3n-3 0.75 ± 0.08 0.76 ± 0.07
Arachidonique (AA) 20 :4n-6 16.14± 1.58 17.53 ±1.75Arachidonic (AA) 20: 4n-6 16.14 ± 1.58 17.53 ± 1.75
Eisopentaenoique (EPA) 20 :5n-3 0.86 ±0.03 1.21 ±0.09**Eisopentaenoic (EPA) 20: 5n-3 0.86 ± 0.03 1.21 ± 0.09 **
Docosapentaenoique (DPA) 22 :5n-3 0.63 ±0.05 0.74 ±0.05Docosapentaenoic (DPA) 22: 5n-3 0.63 ± 0.05 0.74 ± 0.05
Docosahexanoique (DHA) 22 :6n-3 3.85 ±0.22 4.48 ±0.21 *Docosahexanoic (DHA) 22: 6n-3 3.85 ± 0.22 4.48 ± 0.21 *
SFA Total 29.07 ±0.63 27.37 ±0.60SFA Total 29.07 ± 0.63 27.37 ± 0.60
MUFA Total 23.49 ±1.41 22.43 ±1.84MUFA Total 23.49 ± 1.41 22.43 ± 1.84
PUFA Total 47.25 ±1.56 50.03 ±2.12PUFA Total 47.25 ± 1.56 50.03 ± 2.12
Total n-3 6.17 ±0.24 7.21 ±0.27**Total n-3 6.17 ± 0.24 7.21 ± 0.27 **
Total n-6 41.08 ±1.38 42.82 ±1.98 n-3 : n-6 ratio 0.15 ±0.00 o.π±o.oi **Total n-6 41.08 ± 1.38 42.82 ± 1.98 n-3: n-6 ratio 0.15 ± 0.00 o.π ± o.oi **
Tableau 2 (*: P < 0.05, **: P < 0.01 vs. ACN-free) Table 2 (*: P <0.05, **: P <0.01 vs. ACN-free)
SFA : acides gras saturés SFA: saturated fatty acids
PUFA : acides gras polyinsaturés PUFA: polyunsaturated fatty acids
MUFA : acides gras monoinsaturés ACN-free ACN-rich MUFA: monounsaturated fatty acids ACN-free ACN-rich
(n- -15) (n = 10)  (n--15) (n = 10)
Lipides du sang (g/L) Blood lipids (g / L)
Cholestérol Total 0.39 ±0.02 0.42 ±0.02 Cholesterol Total 0.39 ± 0.02 0.42 ± 0.02
Cholestérol HDL 0.32 ±0.01 0.35 ±0.02 HDL cholesterol 0.32 ± 0.01 0.35 ± 0.02
Acides gras (% des acides gras totaux) Fatty acids (% of total fatty acids)
Myristique 14 :0 1.03 ±0.08 1.09 ±0.08 Myristic 14: 0 1.03 ± 0.08 1.09 ± 0.08
Palmitique 16 :0 22.65 ±0.27 22.96 ±0.56Palmitic 16: 0 22.65 ± 0.27 22.96 ± 0.56
Stearique 18 :0 7.73 ±0.45 8.00 ±0.67Stearic 18: 0 7.73 ± 0.45 8.00 ± 0.67
Olieique 18 :ln-9 11.29 ±0.75 11.18 ± 0.61Olieic 18: ln-9 11.29 ± 0.75 11.18 ± 0.61
Linoleique (LA) 18 :2n-6 20.29 ±0.42 19.75 ±0.77 α-linolenique (ALA) 18 :3n-3 0.48 ±0.06 0.36 ±0.03Linoleic (LA) 18: 2n-6 20.29 ± 0.42 19.75 ± 0.77 α-Linolenic (ALA) 18: 3n-3 0.48 ± 0.06 0.36 ± 0.03
Arachidonique (AA) 20 :4n-6 18.83 ±1.11 17.05 ± 1.08Arachidonic (AA) 20: 4n-6 18.83 ± 1.11 17.05 ± 1.08
Eisopentaenoique (EPA) 20 :5n-3 1.31 ±0.07 1.64 ±0.09*Eisopentaenoic (EPA) 20: 5n-3 1.31 ± 0.07 1.64 ± 0.09 *
Docosapentaenoique (DPA) 22 :5n-3 0.90 ±0.05 0.87 ±0.05Docosapentaenoic (DPA) 22: 5n-3 0.90 ± 0.05 0.87 ± 0.05
Docosahexanoique (DHA) 22 :6n-3 4.93 ±0.13 5.44 ±0.25 *Docosahexanoic (DHA) 22: 6n-3 4.93 ± 0.13 5.44 ± 0.25 *
SFA Total 31.43 ±0.57 32.04 ±0.88SFA Total 31.43 ± 0.57 32.04 ± 0.88
MUFA Total 19.86 ±1.07 20.48 ±1.31MUFA Total 19.86 ± 1.07 20.48 ± 1.31
PUFA Total 48.52± 1.15 46.82 ±1.64PUFA Total 48.52 ± 1.15 46.82 ± 1.64
Total n-3 7.62 ±0.25 8.32 ±0.36Total n-3 7.62 ± 0.25 8.32 ± 0.36
Total n-6 40.90 ±1.14 38.50 ±1.43 n-3 : n-6 ratio 0.19 ±0.01 0.22 ±0.01 *Total n-6 40.90 ± 1.14 38.50 ± 1.43 n-3: n-6 ratio 0.19 ± 0.01 0.22 ± 0.01 *
Tableau 3 (*: P < 0.05 vs. ACN-free + Huile Palme) Table 3 ( * : P <0.05 vs. ACN-free + Palm Oil)
SFA : acides gras saturés SFA: saturated fatty acids
PUFA : acides gras polyinsaturés PUFA: polyunsaturated fatty acids
MUFA : acides gras monoinsaturés ACN-free ACN-rich MUFA: monounsaturated fatty acids ACN-free ACN-rich
(n- = 18) (n = 11)  (n = 18) (n = 11)
Lipides du sang (g/L) Blood lipids (g / L)
Total Cholestérol 0.37 ±0.01 0.35 ±0.02  Total Cholesterol 0.37 ± 0.01 0.35 ± 0.02
HDL Cholestérol 0.31 ±0.01 0.28 ±0.02  HDL Cholesterol 0.31 ± 0.01 0.28 ± 0.02
Acides gras (% des acides gras totaux) Fatty acids (% of total fatty acids)
Myristique 14 :0 0.99 ±0.05 0.82 ±0.08 Myristic 14: 0 0.99 ± 0.05 0.82 ± 0.08
Palmitique 16 :0 22.39 '±0.26 21.91 ±0.73Palmitic 16: 0 22.39 '± 0.26 21.91 ± 0.73
Stearique 18 :0 7.95 ±0.36 7.94 ±0.52Stearic 18: 0 7.95 ± 0.36 7.94 ± 0.52
Olieique 18 :ln-9 9.35 ±0.34 10.07 ±0.44Olieic 18: ln-9 9.35 ± 0.34 10.07 ± 0.44
Linoleique (LA) 18 :2n-6 21.96 i ±0.63 20.85 ±0.76 α-linolenique (ALA) 18 :3n-3 0.38 ±0.03 0.43 ±0.03Linoleic (LA) 18: 2n-6 21.96 i ± 0.63 20.85 ± 0.76 α-linolenic (ALA) 18: 3n-3 0.38 ± 0.03 0.43 ± 0.03
Arachidonique (AA) 20 :4n-6 14.45 ±0.50 12.86 ±0.88Arachidonic (AA) 20: 4n-6 14.45 ± 0.50 12.86 ± 0.88
Eisopentaenoique (EPA) 20 :5n-3 4.11 ±0.18 5.09 ±0.38*Eisopentaenoic (EPA) 20: 5n-3 4.11 ± 0.18 5.09 ± 0.38 *
Docosapentaenoique (DPA) 22 :5n-3 1.36 ±0.06 1.56 ±0.08*Docosapentaenoic (DPA) 22: 5n-3 1.36 ± 0.06 1.56 ± 0.08 *
Docosahexanoique (DHA) 22 :6n-3 7.74 ±0.31 9.00 ±0.30 **Docosahexanoic (DHA) 22: 6n-3 7.74 ± 0.31 9.00 ± 0.30 **
SFA Total 31.33 ±0.48 30.68 ±1.01SFA Total 31.33 ± 0.48 30.68 ± 1.01
MUFA Total 16.83 ±0.62 17.68 ±0.99MUFA Total 16.83 ± 0.62 17.68 ± 0.99
PUFA Total 51.64 ±1.00 51.47 ±1.60PUFA Total 51.64 ± 1.00 51.47 ± 1.60
Total n-3 13.60 '±0.46 16.07 ±0.60**Total n-3 13.60 '± 0.46 16.07 ± 0.60 **
Total n-6 38.04 ±0.94 35.39 ±1.59 n-3 : n-6 ratio 0.36 ±0.02 0.47 ±0.36**Total n-6 38.04 ± 0.94 35.39 ± 1.59 n-3: n-6 ratio 0.36 ± 0.02 0.47 ± 0.36 **
Tableau 4 (*: P < 0.05, **: P < 0.01 vs. ACN-free + n-3) Table 4 (*: P <0.05, **: P <0.01 vs. ACN-free + n-3)
SFA : acides gras saturés SFA: saturated fatty acids
PUFA : acides gras polyinsaturés PUFA: polyunsaturated fatty acids
MUFA : acides gras monoinsaturés MUFA: monounsaturated fatty acids
Conclusion Conclusion
Une notable augmentation de l'EPA et du DHA est observée. Les anthocyanines ont un net effet sur les oméga-3, mais aucun effet significatif sur les oméga-6. La seule différence entre les deux groupes de rats étant les apports en anthocyanines, c'est à ces substances que l'on doit attribuer l'effet sur les oméga-3. Il faut noter que dans ces expériences, les apports en ALA étaient identiques dans les groupes supplémentés ou pas en anthocyanines. A notable increase in EPA and DHA is observed. Anthocyanins have a clear effect on omega-3s, but no significant effect on omega-6. The only difference between the two groups of rats being the contributions of anthocyanins, it is to these substances that we must attribute the effect on omega-3. It should be noted that in these experiments ALA contributions were identical in groups supplemented or not with anthocyanins.

Claims

REVENDICATIONS
1. Utilisation d'au moins un acide gras du groupe oméga-3 choisi parmi l'acide α-linolénique et l'acide stéaridonique et d'au moins un polyphénol, en tant qu'agent augmentant la synthèse endogène d'acide éicosapentaénoïque et d'acide docosahexaénoïque, pour la préparation d'une composition alimentaire, diététique ou pharmaceutique destinée à être administrée à un être humain ou à un animal. Use of at least one omega-3 fatty acid selected from α-linolenic acid and stearidonic acid and at least one polyphenol as an agent for increasing the endogenous synthesis of eicosapentaenoic acid and of docosahexaenoic acid, for the preparation of a dietary, dietetic or pharmaceutical composition intended to be administered to a human being or to an animal.
2. Utilisation selon la revendication 1 , caractérisée en ce que le polyphénol est choisi parmi l'apigénine, la lutéoline, l'acide chlorogénique, l'acide caféique, l'acide férulique, les acides coumariques, l'acide hydroxycinnamique, l'acide salicylique, l'acide gallique, la quercétine, l'eriodyctiol, la catéchine, l'épicatéchine, l'epigallocatéchine gallate, l'isorhamnétine, le kaempherol, l'hesperétine, la naringénine, la phlorétine, l'entérolactone, l'entérodiol, l'oleuropéine, l'hydroxytyrosol, le resvératrol, la myricétine, la rutine, les acides phénoliques, les stilbènes, les flavonoïdes et les lignanes. 2. Use according to claim 1, characterized in that the polyphenol is chosen from apigenin, luteolin, chlorogenic acid, caffeic acid, ferulic acid, coumaric acids, hydroxycinnamic acid, salicylic acid, gallic acid, quercetin, eriodyctiol, catechin, epicatechin, epigallocatechin gallate, isorhamnetin, kaempherol, hesperetin, naringenin, phloretin, enterolactone, enterodiol, oleuropein, hydroxytyrosol, resveratrol, myricetin, rutin, phenolic acids, stilbenes, flavonoids and lignans.
3. Utilisation selon la revendication 1 ou la revendication 2, caractérisée en ce que ledit polyphénol est une anthocyanine. 3. Use according to claim 1 or claim 2, characterized in that said polyphenol is an anthocyanin.
4. Utilisation selon la revendication 3, caractérisée en ce q ue ladite anthocyanine est choisie parmi la cyanidine, la delphidine, la malvidine, la peonidine, la pélargonidine et la pétunidine. 4. Use according to claim 3, characterized in that said anthocyanin is selected from cyanidine, delphidine, malvidine, peonidine, pelargonidine and petunidine.
5. Utilisation selon l'une quelconque des revendications 1 à 4, caractérisée en ce que ladite composition comprend en outre un composé choisi parmi les vitamines, les sels minéraux et les oligo-éléments. 5. Use according to any one of claims 1 to 4, characterized in that said composition further comprises a compound selected from vitamins, mineral salts and trace elements.
6. Utilisation selon l'une quelconque des revendications 1 à 5, caractérisée en ce que ladite composition se trouve sous la forme de granules, de poudre, de liquide, de semi-liquide. 6. Use according to any one of claims 1 to 5, characterized in that said composition is in the form of granules, powder, liquid, semi-liquid.
7. Utilisation selon l'une quelconque des revendications 1 à 6, caractérisée en ce que la composition alimentaire ou diététique est une huile, une margarine, un yaourt, un fromage, un pain, une biscotte, un gâteau, un biscuit, un substitut de repas, une crème, une barre chocolatée, une barre de céréales, une compote à base de fruits. 7. Use according to any one of claims 1 to 6, characterized in that the food or dietetic composition is an oil, a margarine, a yogurt, a cheese, a bread, a rusk, a cake, a biscuit, a substitute a meal, a cream, a chocolate bar, a cereal bar, a compote made from fruit.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8168611B1 (en) 2011-09-29 2012-05-01 Chemo S.A. France Compositions, kits and methods for nutrition supplementation
US8183227B1 (en) 2011-07-07 2012-05-22 Chemo S. A. France Compositions, kits and methods for nutrition supplementation

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX370090B (en) 2013-02-01 2019-10-25 Centro De Investig En Alimentacion Y Desarrollo A C Method and system for the integral treatment of wastewater from the maize industry.
PL3054777T3 (en) * 2013-10-07 2018-10-31 Zinzino Ab Edible lipid composition comprising stearidonic acid and olive oil
EP4312576A1 (en) * 2022-05-12 2024-02-07 Industrial Técnica Pecuaria S.A. Hydroxytyrosol for processing animal by-products

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004004638A2 (en) * 2002-07-02 2004-01-15 Galileo Pharmaceuticals, Inc. Compositions and methods for reduction of inflammatory symptoms and/or biomarkers in female subjects
WO2005112960A1 (en) * 2004-05-19 2005-12-01 Bionovate Limited Treatment for asthma and arthritis and othe inflammatory diseases
CN101091504A (en) * 2007-06-12 2007-12-26 上海地源食品有限公司 Green tea oil, and preparation method
FR2912918A1 (en) * 2007-02-27 2008-08-29 Persee Medica Soc Par Actions Use of polyunsaturated fatty acids and flavonoids, as active agent for simultaneous, sequential or separate use for the preparation of a composition for the prevention and/or treatment of headache
WO2008136739A1 (en) * 2007-05-04 2008-11-13 Jana Pickova Compound feed for aquaculture
CN101322743A (en) * 2008-08-01 2008-12-17 李翔 Formulation capable of repairing lesion and damnification of eye and improving asthenopia and preparation thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2199010A1 (en) 1995-07-04 1997-01-23 Osamu Igarashi Food composition containing balancing agent for .omega.-6 and .omega.-3 unsaturated fatty acids
US6423365B1 (en) * 1998-12-11 2002-07-23 Board Of Trustees Of Michigan State University Method and compositions producing cherry derived products
US20090202668A1 (en) * 2006-06-07 2009-08-13 Hugenholtz Paul G Use of a polyphenol in the treatment of the metabolic syndrome and endothelial dysfunction or other vascular sequellae
US20090264520A1 (en) 2008-04-21 2009-10-22 Asha Lipid Sciences, Inc. Lipid-containing compositions and methods of use thereof
DE202008016372U1 (en) * 2008-12-11 2009-04-16 Orthomol Pharmazeutische Vertriebs Gmbh Vitamin-containing composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004004638A2 (en) * 2002-07-02 2004-01-15 Galileo Pharmaceuticals, Inc. Compositions and methods for reduction of inflammatory symptoms and/or biomarkers in female subjects
WO2005112960A1 (en) * 2004-05-19 2005-12-01 Bionovate Limited Treatment for asthma and arthritis and othe inflammatory diseases
FR2912918A1 (en) * 2007-02-27 2008-08-29 Persee Medica Soc Par Actions Use of polyunsaturated fatty acids and flavonoids, as active agent for simultaneous, sequential or separate use for the preparation of a composition for the prevention and/or treatment of headache
WO2008136739A1 (en) * 2007-05-04 2008-11-13 Jana Pickova Compound feed for aquaculture
CN101091504A (en) * 2007-06-12 2007-12-26 上海地源食品有限公司 Green tea oil, and preparation method
CN101322743A (en) * 2008-08-01 2008-12-17 李翔 Formulation capable of repairing lesion and damnification of eye and improving asthenopia and preparation thereof

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
CUSH ET AL: "407 ARCHER STUDY: AN OPEN-LABEL TRIAL OF CHERRY EXTRACT (ANTHOCYANINS) IN OSTEOARTHRITIS OF THE KNEE", OSTEOARTHRITIS AND CARTILAGE, BAILLIERE TINDALL, LONDON, GB, vol. 15, 1 December 2007 (2007-12-01), pages C221, XP022491491, ISSN: 1063-4584 *
DATABASE WPI Week 200914, Derwent World Patents Index; AN 2009-A99596, XP002606275 *
DE LORGERIL ET AL., AMERICAN HEART JOURNAL, vol. 155, 2008, pages 175 - 181
DE LORGERIL ET AL: "Interactions of wine drinking with omega-3 fatty acids in patients with coronary heart disease: A fish-like effect of moderate wine drinking", AMERICAN HEART JOURNAL, MOSBY- YEAR BOOK INC, US, vol. 155, no. 1, 1 January 2008 (2008-01-01), pages 175 - 181, XP022408119, ISSN: 0002-8703 *
DI GIUSEPPE ET AL., AM J CLIN NUTR, vol. 89, 2009, pages 1 - 9
GUIRAUD ET AL., BRITISH JOURNAL OF NUTRITION, vol. 100, 2008, pages 1237 - 1244
See also references of EP2453888A1
TOUFEKTSIAN ET AL., J NUTR, vol. 138, 2008, pages 747 - 752

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8183227B1 (en) 2011-07-07 2012-05-22 Chemo S. A. France Compositions, kits and methods for nutrition supplementation
US8168611B1 (en) 2011-09-29 2012-05-01 Chemo S.A. France Compositions, kits and methods for nutrition supplementation
US8545896B2 (en) 2011-09-29 2013-10-01 Chemo S. A. France Compositions, kits and methods for nutrition supplementation

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